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Strawberry Letter: Dating The Best Friend’s Ex

Dear Steve Harvey and Shirley,

I am writing to get your opinion on the matter of friends dating their best friends ex. I am a 43-year-old woman who has a really good male friend of 30 years. We have always been very close and always took good care of each other. Over the past 4 years, so many of our mutual friends have told us that we have an amazing chemistry and a very strong bond, but we continued to say we are just friends.

Friends would hear us say “Love You” and interpret that to mean that there was more between us then we were saying. One day, 2 years ago the words “I Love You” sounded and felt different. We both knew what was happening and at that time we expressed our love for each other and began to take our friendship to another level. After much conversation about our future, after much expression of our love and after much love-making, he realized that he couldn’t pursue a relationship with me because I dated his best male friend in High School. They are still best friends today and this best friend has been married for 17 years with 3 children in that marriage.

I didn’t understand why the sudden change, we discussed this in the very beginning and he said that it wouldn’t be an issue. Apparently the best friend still has feelings for me and he tells him this on a regular basis. He feels that as long as he knows how the best friend feels about me right now is what matters. He feels as if he would be betraying a childhood friendship. Needless to say I was heartbroken! I told him that I don’t really consider myself the ex of the best friend because we were just children at the time we dated, but I will respect his decision.

I have been trying to move on with my life but it has been so difficult. I don’t see him very often but when I do we share some very passionate and intimate moments, then we go back to trying to stay away from each other. Every morning he sends me a good morning text and every night he sends good night I love you. It is very clear that he loves me but he has chosen his friendship over our love. I really feel like we could have a great love and relationship.

My question to you is, should this even be an issue? Am I still considered to be the ex of his best friend although it was 26 years ago when we dated? Do you think that he should talk to the best friend about the situation?


Between Friends

Listen to Steve and Shirley comment on this letter below:


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